Total synthesis of (S)-(+)-imperanene.: Effective use of regio- and enantioselective intramolecular carbon-hydrogen insertion reactions catalyzed by chiral dirhodium(II) carboxamidates

被引：50

作者：

Doyle, MP ^{[1
]}

Hu, WH ^{[1
]}

Valenzuela, MV ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 09期

关键词：

D O I：

10.1021/jo016220s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of (S)-(+)-imperanene, a natural product found in Chinese medicine, has been completed in 12 steps from a commercially available cinnamic acid. The key step is highly enantioselective carbon-hydrogen insertion from a diazoacetate using a chiral dirhodium(II) carboxamidate catalyst. An elimination process essential to the construction has been optimized to avoid intramolecular Friedel-Crafts alkylation.

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收藏

页码：2954 / 2959

页数：6

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